3-Aminobenzamide → 2-(3-Carbamoylphenylamino)-2-(4-(2-(3-(3-cyanophenyl)-1-methylureido)ethyl)phenyl)acetic acid

HRID 735646Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:24])[N:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=2)[CH3:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([NH2:31])=[O:30].O.[C:36]([OH:40])(=[O:39])[CH:37]=O>>[C:29]([C:28]1[CH:27]=[C:26]([NH:25][CH:37]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][N:11]([CH3:12])[C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)=[O:24])=[CH:16][CH:17]=2)[C:36]([OH:40])=[O:39])[CH:34]=[CH:33][CH:32]=1)(=[O:30])[NH2:31]

Participants

Reactant 3

HCID 16453-Aminobenzamide

HCID 15620607Glyoxylic acid, monohydrate

HCID 578426104-(2-(3-(3-Cyanophenyl)-1-methylureido)ethyl)phenylboronic acid

Product 1

HCID 578425772-(3-Carbamoylphenylamino)-2-(4-(2-(3-(3-cyanophenyl)-1-methylureido)ethyl)phenyl)acetic acidYield 64%

Procedure

Using a procedure analogous to that used to prepare 2D, 23D (170 mg, 0.52 mmol) was reacted with 3-aminobenzamide and glyoxylic acid monohydrate to afford 58A (157 mg, 64%) as an oil. MS (ESI) m/z 472.3 (M+H)+.

Sources & evidence

ORD record: ord-5a03452fac2b4226b0a02d195bbb4033
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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